Insights from Dana
How to Take Time Off Without Killing Your Business

Part Two: Four Steps to Successfully Taking Time Off

Once upon a time, like oh so many business owners, I worked endless hours, days, nights, and weekends. I felt guilty and I missed my family, but I thought it was what I had to do for my business to succeed. 

Then I decided that there really had to be a better way and now my life is wildly different. 

Now I take three day weekends as a rule – Friday, Saturday, and Sunday are my regular days off.

I go on an extended vacation twice a year (not counting events, conventions, work related travel, or pandemics).

I take a lot of time off because when I’m working with clients we do a lot of deep diving and strategic thinking. It’s my job to hold space to help my clients see the world from a different perspective, which means that I spend a lot of time in focused, intimate conversations, and I need time and space to let that stuff go. 

I need room to reset my brain so that I can keep the flow of new ideas coming. 

I learned how to build a business that supports me in living a life I love to live, but first I had to recondition my brain and my nervous system so that work wasn’t my default setting anymore.

I had to learn how to stop working all the damn time and take time off, and I had to learn how to do it without killing my business. I’ve walked hundreds of clients through this process so that they can actually take time off work, live more fulfilling lives, and lead their businesses from a place of vision and inspiration to ongoing and sustainable success.

Here’s how…




Before you can put a plan in place so that you can take time off, you have to decide that you’re actually going to do it. Even though it will probably be challenging for you personally, and maybe even a little anxiety-inducing, you have to commit to taking the time to take care of yourself so that you can take care of business.

For a lot of business owners, that’s harder than it sounds. It’s easier to commit to grinding ourselves to dust than it is to take time off. 

Your First Step: Plan your vacation. Decide where you’re going, when, and if you want anyone to come with you. Put it on the calendar. You don’t have to book tickets or make reservations yet, but you have to know what the target is, and you have to commit to making it happen. 

If you know you have a hard time taking time away from work, get more detailed with your plans. Talk the plan up with your partner or bff. Book the damn tickets. The harder it is to cancel, the better. You don’t need to just plan for some down time, you need to actually take it.


Whether you work with contractors like I do, or you have a dedicated team of employees, you need to have a plan in place to ensure that the bases are covered in your absence. Having an action plan in place sets your team up for success so that they can take care of the essentials while you’re away. 

Training your team isn’t just teaching your people to follow processes and procedures by rote. 

You need to train your team members to produce results so that they understand their role in your business and the outcomes they’re responsible for producing. 

And then you need to trust them to get the job done. 

Your job isn’t to micromanage every step. Your job is to clarify what needs to be done and then provide the support and resources for your people to get from A to Z. 

When you train your team to produce results, and they’re comfortable with what that looks like, then when you’re out of the picture, they just keep doing what they’ve been doing – making it happen. 

What are the things that absolutely have to happen while you’re gone? 

The key here is actually defining what is essential. There are things that you want to happen but those are different from the things that need happen.

Your Second Step: Make a list of all of your active initiatives and projects and identify the essential tasks that need to be covered. Before you can confidently and comfortably start taking time off, you need to identify the essential tasks you’ve been responsible for that need to happen while you’re gone, and then delegate those activities based on the results that you would be producing. And you know that you can trust them to do it, because you’ve been trusting them all along. 


Beyond identifying what has to be done, you need to have a communication strategy so that your team knows what level of communication is expected, how to communicate with one another, with your clients, and how to communicate (or not) with you. 

The reality is that for some business owners, you can’t just leave your business for a week without checking in. Or maybe you’re finally taking off on an extended vacation and you want your team to send you weekly updates while you’re away. Whether you’re taking off for a long weekend or planning a month-long getaway, a clear communication strategy helps keep your team on the same page and working together.

The devil is in the details.

How are you going to communicate with your team while you’re away?

In most circumstances, email is usually the best way to go because then you have an established chain of communication and a document trail.  Plan a midweek check-in so that you know how things are going and your team has time to adjust the plan if needed.

If you’re only taking a week off, do not plan more than one check-in.

If you’re going away for longer, consider when it is most appropriate to have your team follow up with you. Does having your team check-in with you in the middle of the week and at the end of the week give you the awareness you want and the time you need to respond if absolutely necessary?

Remember, you’re not working, you’re just staying informed. Plan accordingly.

What happens if there is an emergency?

Leave an itinerary and a contact number with your team, but make sure that everyone is crystal clear that it is only to be used in case of an emergency. And then define what an emergency looks like.

One of the things I teach my clients to do before taking time off is to walk your team through some different scenarios and how to handle them in your absence.  

What are you worried about? 

Identify your concern and the specific circumstances that you’re worried about, and then ask your team how they would handle that scenario.Come up with a plan for what would happen if those particular concerns were to come to life. 

Then ask what they’re worried about dealing with while you’re gone and create a contingency plan so that they feel supported and resourced to manage successfully while you’re away.

Remember, as much as you can try to predict the future, no matter how prepared you are for any number of outcomes, there is always the possibility that something will happen that you didn’t think about at all. 

This is where your communication strategy and emergency contact information comes into play. Make sure your team is crystal clear on what constitutes an emergency and under what circumstances you want them to dial that emergency number. 

Your Third Step: Create your communication strategy and review it with your team. Remember to include when, how, and why you want your team to check in with you, and what details you want them to include when they do. Define what constitutes an emergency. Work through some challenging scenarios together.  


It’s really hard to go from working five, six, or seven days a week to taking three weeks off. 

Neither your or your team are prepared for that (yet). 

If you tried to take a few weeks off right now, you would probably spend the whole time fielding phone calls and checking your email instead of being present in the moment and on vacation. 

If that sounds familiar, you aren’t the only one. I’ve had clients who had never so much as taken a weekend off since starting their business. 

Sadly, it’s not uncommon. This is why you need to start practicing taking time away. 

Phase One: Practice taking time off by taking a full day off.

That means 24 hours. No email, no messages, no phone calls, no checking that thread on Slack just in case.  Taking 24 hours off means a total ban on business and you need to implement that ban at least once a week.

Phase Two: Then, when you’re really and truly taking a whole day away from work, it’s time to start taking an entire weekend off.

Your weekend can be whenever you want it to be. Some of my clients work in industries that are busiest on the weekend, so their “weekend” falls on Monday and Tuesday. On your weekend off, your only job is to enjoy yourself. Spend time with your family, putter in your garden, or stay in bed and read a book all day if that’s what you want to do. But no work. 

Phase Three: The next exercise is to take a long weekend off, and I don’t mean Memorial Day or Labor Day. I mean that, periodically, you are going to take an extra day off while your team is working, so that they can practice too.

When you come back from your long weekend, it’s time to check in with your team and refine your plan. 

What worked? Talk about what went well and why it worked. Celebrate your team.

What didn’t work? Were there any emergencies? Were clients left hanging? Were there decisions that needed to be made that your team wasn’t empowered to make without you? 

Walk through each issue with your team, identify and provide any additional tools or resources they might need, and create a plan of action going forward so that you all feel confident that your team is set for success.

Phase Four: Take a week off work. Barring any emergencies, stick to your communication strategy. Rest. Relax. Get into shenanigans. Eat good food. Do whatever you want – but no work.

When you go back to work, review what worked and what didn’t work again with your team. Continue checking in to refine your plans and enhance your processes every time you take time away, you might be surprised at the ideas your team comes up with.

Your team needs time off too. 
To create a culture where your people feel good about taking time off so that they can do their best work and not burn out, you have to model taking time off, so that you can do your best work out and not burn out. Otherwise, a team member taking time off can be misinterpreted by the rest of the team as that individual being less committed, checked out, or selfish.

We all need time away from work to rest and refuel.
You can avoid fostering a culture of burnout and resentment, even unintentionally, by actively valuing and prioritizing time off for yourself and your team. 

To Recap Four Steps to Successfully Taking Time Off (Without Killing Your Business)…

  1. Commit to Taking Time Off. Make the decision and start planning your time away – where do you want to go? When? With who? The more details the more likely you are to follow through.
  1. Make an Action Plan. Identify the essential tasks that need to be covered in your absence and delegate accordingly. Trust your team.
  1. Create a Communication Strategy. Set expectations for when and why you want your team to get in touch. Make it clear to everyone – yourself included – that you aren’t 
  2. available under any circumstances except an emergency. Define emergency. 
  1. Practice Makes Perfect. Put your Action Plan and Communication Strategy in place and get away from work 24 hours. 48 hours. A long weekend. A week. Soon you’ll be taking a real vacation. Imagine the possibilities.
dana corey signature

Like it? Share it!

Are You an Overloaded CEO?

Find out which Swamped Business Owner Syndrome is keeping you inundated, stressed, and exhausted.

Take this personalized business assessment to find your strategic next steps.